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- Barbier_reaction abstract "The Barbier reaction is an organic reaction between an alkyl halide and a carbonyl group as an electrophilic substrate in the presence of magnesium, aluminium, zinc, indium, tin or its salts. The reaction product is a primary, secondary or tertiary alcohol. The reaction is similar to the Grignard reaction but the crucial difference is that the Barbier reaction is a one-pot synthesis whereas a Grignard reagent is prepared separately before addition of the carbonyl compound. Barbier reactions are nucleophilic addition reactions that usually take place with relatively inexpensive and water insensitive metals or metal compounds in contrast to Grignard reagents or organolithium reagents. For this reason it is possible in many cases to run the reaction in water which makes the procedure part of green chemistry. The Barbier reaction is named after Victor Grignard's teacher Philippe Barbier.Examples of Barbier reactions are the reaction of propargylic bromide with butanal with zinc metal in water:With a substituted alkyne instead of a terminal alkyne the allene product is favouredthe intramolecular Barbier reaction with samarium(II) iodide:the reaction of an allyl bromide with formaldehyde in THF with indium powder:The Barbier reaction is accompanied by an allylic rearrangement to a terminal alkeneor another allyl bromide in a reaction with benzaldehyde and zinc powder in water:The observed diastereoselectivity for this reaction is erythro : threo = 83 : 17".
- Barbier_reaction thumbnail Samariumiodide.jpg?width=300.
- Barbier_reaction wikiPageExternalLink barbier.html.
- Barbier_reaction wikiPageID "2322053".
- Barbier_reaction wikiPageRevisionID "542614771".
- Barbier_reaction hasPhotoCollection Barbier_reaction.
- Barbier_reaction subject Category:Addition_reactions.
- Barbier_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Barbier_reaction subject Category:Free_radical_reactions.
- Barbier_reaction subject Category:Name_reactions.
- Barbier_reaction type AdditionReaction113427356.
- Barbier_reaction type AdditionReactions.
- Barbier_reaction type ChemicalProcess113446390.
- Barbier_reaction type ChemicalReaction113447361.
- Barbier_reaction type FreeRadicalReactions.
- Barbier_reaction type NameReactions.
- Barbier_reaction type NaturalProcess113518963.
- Barbier_reaction type PhysicalEntity100001930.
- Barbier_reaction type Process100029677.
- Barbier_reaction comment "The Barbier reaction is an organic reaction between an alkyl halide and a carbonyl group as an electrophilic substrate in the presence of magnesium, aluminium, zinc, indium, tin or its salts. The reaction product is a primary, secondary or tertiary alcohol. The reaction is similar to the Grignard reaction but the crucial difference is that the Barbier reaction is a one-pot synthesis whereas a Grignard reagent is prepared separately before addition of the carbonyl compound.".
- Barbier_reaction label "Barbier reaction".
- Barbier_reaction label "Barbier-Reaktion".
- Barbier_reaction label "Barbier-reactie".
- Barbier_reaction label "Barbier反應".
- Barbier_reaction label "Reacción de Barbier".
- Barbier_reaction label "Réaction de Barbier".
- Barbier_reaction label "バルビエ反応".
- Barbier_reaction sameAs Barbier-Reaktion.
- Barbier_reaction sameAs Reacción_de_Barbier.
- Barbier_reaction sameAs Réaction_de_Barbier.
- Barbier_reaction sameAs バルビエ反応.
- Barbier_reaction sameAs Barbier-reactie.
- Barbier_reaction sameAs m.073prn.
- Barbier_reaction sameAs Q807848.
- Barbier_reaction sameAs Q807848.
- Barbier_reaction sameAs Barbier_reaction.
- Barbier_reaction wasDerivedFrom Barbier_reaction?oldid=542614771.
- Barbier_reaction depiction Samariumiodide.jpg.
- Barbier_reaction isPrimaryTopicOf Barbier_reaction.
